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33 Winding Trail, Whispering Pines, NC 28327 – photo 1 of 23: 33 Winding Trail-211 / 23

$389,000

3 bd · 2 ba · 2,008 sq ft

33 Winding Trail

Whispering Pines, NC, 28327 · Whispering Winds

Listed 122 days ago

Hive MLSListed by Keller Williams Pinehurst

About this home

A rare townhouse find in coveted Whispering Pines! This single-level three-bedroom, two-full-bath townhome has been exceptionally maintained by the original owners. The open floor plan of the living and dining area offers a flexible layout and design options, complete with a built-in bookcase and a gas fireplace. The eat-in kitchen has a large bay window, tile floors, ample countertop space, plenty of storage and French doors leading to the bonus ''Carolina'' room. The large primary bedroom has an en-suite bath with a walk-in shower, separate commode closet, and a nicely sized walk-in closet. The second full bathroom features tile floors, a bathtub/shower combination and a linen closet for additional storage. Both bathrooms have solar tubes which bring in great natural light. Other features include: a private concrete back patio with a retractable awning, pull-down stairs in the two car garage to access bonus attic storage space. Mechanical updates: New roof installed in 2024 New 3-ton Trane air conditioner and gas furnace installed in 2023 with extended warranties Septic pumped in 2025 Enjoy a true lock-and-leave lifestyle in a tight-knit community. Whispering Winds HOA takes care of the landscaping and lawn maintenance as part of your HOA dues, allowing you more time to relax and enjoy the area. This exceptional property also boasts an unbeatable location. Conveniently situated just 10 minutes from Pinehurst Resort -- known as the ''Home of American Golf'' -- and only a few miles from the fine dining, boutique shopping, and entertainment of Southern Pines. For active-duty military families, 33 Winding Trail is located less than 30 minutes from Fort Bragg. For weekend getaways, you are approximately 2.5 hours from both the Appalachian Mountains and the beautiful North Carolina coast. Don't miss this opportunity--schedule your showing today!

Facts

Type
Townhouse
Year built
2004
Garage
2 spaces
HOA
$3,000 / annually
Community
Whispering Winds
County
Moore
MLS #
100576112

Features

Inside

  • Master Downstairs
  • Walk-in Closet(s)
  • Tray Ceiling(s)
  • High Ceilings
  • Entrance Foyer
  • Ceiling Fan(s)
  • Blinds/Shades
  • Walk-In Closet(s)
  • Carpet
  • Ceramic Tile
  • Built-In Microwave
  • Refrigerator
  • Dishwasher
  • Electric Range

Outside

  • Interior Lot

Community

  • Maintenance Common Areas
  • Maintenance Grounds
  • Management

Parking

  • Garage Faces Front
  • Concrete
  • Garage

Heating & cooling

  • Propane
  • Gas Pack
  • Heat Pump
  • Fireplace(s)
  • Electric
  • Forced Air
  • Central Air
  • Ceiling Fan(s)

Schools

Elementary
McDeeds Creek Elementary
Middle
New Century Middle
High
Union Pines High

As listed in the MLS (Moore County Schools). School assignments can change — confirm with the district for this address.

Monthly payment estimate

$2,771/mo

  • Principal & interest (30-yr fixed)$2,336
  • Property taxes (2026 bill)$185
  • HOA dues$250

Estimate only. Rate is the national 30-year average (7.03% as of Sep 24, 2026, Freddie Mac); your rate depends on your lender. Homeowners and flood insurance aren't included — on the coast they vary a lot by house, so get a quote early.

Buying in Whispering Pines? Local guides

About 33 Winding Trail

33 Winding Trail is a 3-bedroom, 2-bath townhome of about 2,008 square feet, built in 2004 in Whispering Winds, Whispering Pines, Moore County, NC 28327.

At $389,000, it's 22% below the median asking price ($499,000) of the 15 other 3-bedroom listings for sale in Whispering Pines today.

That's about $194 per square foot, compared with a Whispering Pines median of $213.

2 other homes are for sale in Whispering Winds right now (median asking $473,500); 4 homes sold there in the last 12 months at a median of $510,000, typically in about 80 days.

Across ZIP 28327, 160 3-bedroom homes sold in the past year at a median of $325,000.

It has been on the market for 123 days.

Whispering Winds neighborhood guideHomes for sale in Whispering PinesMoore County homes

Buying 33 Winding Trail

  1. See it in person. Pick a time and we'll call to confirm — often same day.
  2. Talk numbers. Tell us what you'd like to offer. It's non-binding — a licensed agent calls you before anything is written.
  3. Have a home to sell first? Our guaranteed sale lets you buy with a firm plan for your current home. How it works

Own a home near 33 Winding Trail? See what it's worth — every online estimate side by side, next to real sales in Whispering Winds.

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Questions about 33 Winding Trail

How much is 33 Winding Trail?

33 Winding Trail is listed at $389,000 (about $194 per square foot) as of September 26, 2026. Status: for sale.

How many bedrooms and bathrooms does 33 Winding Trail have?

3 bedrooms and 2 bathrooms, with about 2,008 square feet.

What neighborhood is 33 Winding Trail in?

Whispering Winds, in Whispering Pines, Moore County, North Carolina.

How long has 33 Winding Trail been on the market?

123 days. Homes in Whispering Winds sold after a median of 80 days over the past year.

What have homes sold for in Whispering Winds?

4 homes sold in Whispering Winds in the last 12 months, at a median price of $510,000.

Does 33 Winding Trail have an HOA fee?

Yes: $3,000 (annually), per the MLS.

When was 33 Winding Trail built?

2004.

Who is the listing broker for 33 Winding Trail?

Keller Williams Pinehurst (MLS #100576112). The Buddy Blake Team can show it to you and answer questions.

Can I tour 33 Winding Trail?

Yes. Tap “Schedule a tour,” pick a time, and we'll call to confirm — or call or text (910) 395-1000.

Listing provided by Keller Williams Pinehurst via Hive MLS.